


Fear Itself

by SherryBaby14



Category: Supernatural
Genre: Abuse, Anal Sex, Dark, Demon Dean Winchester, Demon!Dean, F/M, Forced Orgasm, Kidnapping, Name Calling, Self Harm, Smut, Soulless Sam Winchester, Suicidal Thoughts, Threesome - F/M/M, very dark
Language: English
Status: Completed
Published: 2019-06-20
Updated: 2019-06-20
Packaged: 2020-05-15 10:58:47
Rating: Explicit
Warnings: Rape/Non-Con
Chapters: 3
Words: 12,652
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/19294351
Author URL: https://archiveofourown.org/users/SherryBaby14/pseuds/SherryBaby14
Summary: After picking up a charming man at a bar you discover things are not what they seem





	1. Chapter 1

**Author's Note:**

> THIS IS THE DARKEST THING I'VE EVER DONE. PLEASE DO NOT READ IF IT OFFENDS YOU! IT IS NOT LIKE MY OTHER STUFF!!

Out of character. Those three words ran through your head as you followed the beast of a man up the walkway. It made you smile. Always the good girl, the shy one. Here you were having your first one night stand and man… was he worth it. The chestnut hair, doe eyes, and boy next door charm. You were practically giddy. 

“I hope you keep smiling like that all night.” Sam gave you a wink. 

When you arrived at the front door all your nerves vanished. He was charming. Maybe this wouldn’t be a one night stand. Maybe this would be more. Maybe this would be the one you saw when the veil was lifted from your eyes and you said those two words. I do. 

You would eventually tell him you thought this was going to be a one night stand. The two of you would laugh and make secret jokes about it. 

“You alright?” His eyes squinted and he tilted his head.

Moving way to fast like always you nodded your head. You needed to stop and enjoy this for what it was. A night of fun. Focus on the present, not the future. 

Besides, the man was practically giving you an orgasm with his eyes, you couldn’t wait to find out what the rest of him was capable of. He opened the door and you stepped into the foyer. 

“Where the hell you’ve been?” A blonde sat at a table straight ahead. 

He wasn’t alone. There were four other people with him, shuffling over papers and…was that a knife? 

“Relax Dean.” Sam pulled you next to him and through his arm around your shoulder. “This is Y/N.” 

The guy known as Dean looked shocked. Nobody else at the table even glanced your way. 

“I didn’t know you had roommates.” The bald man looked too old for that term. 

“Dean’s my brother.” Sam started walking you towards the staircase, holding you against him. “I’d introduce you to the rest, but we have better ways to spend our time. Don’t you think?” 

“Maybe I should go.” 

“Don’t say that Y/N.” Sam looked down at you as he guided you up the stairs. “My family is a bit nomadic. Just some out of town guests. Once we’re upstairs you will forget they’re even here.” 

The confidence you were feeling vanished. Sam was walking fast and his grip slid to your waist. He lifted your feet off the ground and before you knew it you were at the top of the stairs. 

“Trust me. I promised a night to remember and I plan on delivering.” He chuckled and looked down at you with the puppy dog eyes. 

You laughed and looked away. He was right. One night stand. You never planned on seeing him again. Push that wedding fantasy away! What did it matter if some strangers thought less of you? 

“Ah, that’s my girl.” Sam squeezed your tight before setting you back down. 

He kept his arm around you as he walked to a room. He pushed the door open and turned on the light to show a normal setup. There was a bed, dressers, average room décor. 

You were taking it in when Sam came up behind you. His large arms draped over, dwarfing you. He was warm and you felt small. He started kissing your neck. It had been so long since anyone touched you this way you relaxed into him. 

His teeth grazed your neck and you rolled your shoulder. He responded by gripping you tighter. It set off a flag. 

“Didn’t we come back here for a drink?” You gave a laugh, but your nerves were in full swing. 

“Well we would have to go back downstairs for that Baby.” Same placed small kisses on your neck between his words. “Do you really want to get to know my grandfather?” 

Shit. He was right about that one. Still something was making your blood cool. 

“Besides, we both know why you really came here with me.” He moved his hands to your hips and started bunching up your dress. 

You immediately grabbed the hem and pulled it back down. 

“Slow down. Maybe we should go over some things first.” You were down for a one night stand, but still expected some romancing. 

Sam responded by biting. Hard. 

You squealed and moved your hands to his head to try and push it off your neck. 

RIPPPPP. Before you could react your dress was shredded into two. 

“WHAT THE HELL?” You pressed your forearm against your bra and put your other hand over your panties. 

“Don’t be a fucking tease.” Sam shoved your back and you fell onto the bed. 

You braced yourself on the edge. His hands went under your knees and lifted you forward. In a manner of seconds you found yourself on all fours on a stranger’s bed in your underwear. 

“STOP!” You tried to stand up, but a large hand went to the small of your back. 

Sam leaned over you, his mouth right next to your ear. 

“Scream like that and my family will come up and join us.” He slid your shoes off before the sound of a belt coming off filled the room. “Or would you like that? Are you greedy for cocks?”

The cool blood you were feeling turned to ice. Tears stung your eyes as your brain struggled to comprehend what was happening. 

“Keep that in mind the next time you feel like yelling.” Sam pushed off of you. 

The sound of his zipper coming down was even louder than the belt. You wanted to run, but were frozen in fear. 

“Let me leave.” It came out in a whisper. 

“I promised a night you wouldn’t forget and I plan on delivering.” Hands were on the waist of your panties. 

“NO.” You grabbed them and fell forward in the same process, pressing your cheek into the mattress and pushing your ass in the air. 

CRACK! The noise registered before the pain flooded your butt cheek. 

“Last warning Y/N.” SLAP! SPANK! “Make another noise and I will go get my brother. Or wait? Are you that kinky? Would you rather it was my grandpa?”

A sob broke free and you dropped your guard. With no resistance Sam slid your panties over your ass. You tried to pin your thighs together but there was no denying you were fully exposed. 

“Much better Y/N.” Sam shuffled behind you, no doubt undressing. 

You needed to push yourself up, crawl away. Do something. You started to rise, when his hand was on your back again. 

“Un-un-un.” He forced you back down. “I decided I like this position. Keep your head on the bed.” 

You did as you were told. More tears and sniffles came. You needed to think of something to do. Some way to end this. 

“I knew you were a smart girl Y/N. That’s why I picked you.” He was taking his time undressing. You didn’t dare look. “Know when to stay quiet, good at following orders. Truthfully I don’t want to share.” 

You heard a dresser drawer open, but you ignored it and pinched your eyes shut. Find a way out. 

“What do you want?” You voice shook with tears and fear. 

“Pretty simple.” The bed dipped behind you and you trembled. “I want to get off. I want to use you for my release. I want you to stay quiet. I want you to stay still. You are a toy for me. One I will play with all night. I do not care about you. Do not for a second think that I do. Now can you cooperate? Be quiet? Stay still? Do what I tell you?” 

“Please don’t.” Your body started to shake and you fisted the sheets. 

“Tsk tsk. Already moving.” One of Sam’s hands grabbed your hip. “Maybe I should just get a sex doll or maybe a dead body?” 

You let out a quiet scream into the comforter. Was that a threat? Was he going to kill you? 

“I should not have said that Y/N. I do not want to hurt you. I promise. I just want to use you. That is all.” You felt his cock brush against your opening. “But if it happens to hurt. I really do not care.” 

Before you had time to process his statement his cock slid up. Your eyes widened with a new fear. 

“PLEASE! NO! I’VE NEVER…” 

“Me either.” He pushed forward. 

Your anal cherry was popped in a second. He slid in with ease and it felt like a fire lit inside your ass. You couldn’t tell if you were screaming out loud or not. 

“You are tight Y/N.” The fire stopped. “I used a ton of lube and barely made it in an inch. Maybe I should have worked you first.” 

An inch? It felt like he was buried in your bowels.

“Oh well.” He plunged in and the burning returned. 

You screamed and sobbed, fisting the sheets tighter. The pain disappeared again, but the phantom of his cock stilled throbbed your insides. You realized you weren’t breathing and tried to gulp in air. Before you could exhale the pain came back. 

You let out another yelp as he filled your rear again. Your body was being split in two, you were sure of it. He was going to murder you with his cock.

“Almost there Y/N.” 

This time when he backed out you did not get a second of relief before he plunged back inside. You were shaking uncontrollably and screaming with abandon. It hurt. It hurt so much.

He did not pull away. Instead he moved deeper. You let out a sob as the burn increased. 

“You are doing so well being quiet.” He shoved in further. “Bite the blanket if you have to.” 

You were quiet? You were screaming! Were you? How the hell did this happen? 

“Beautiful Y/N.” His hips touched your ass cheeks. 

He was all the way in. You couldn’t begin to imagine how deep. Another sob started to form, but you turned your head and bit the blanket. 

“Good job.” Sam moved his hands so one was on each hip. 

He moved his hips back, but his cock barely moved. 

“You are so tight it’s like a vacuum.” He pushed forward and smooshed your cheeks again. “Don’t worry. I’ll figure you out.” 

Sam started pumping and you groaned. It felt like his cock was a stick rubbing fast, trying to start a giant bone fire inside of you. As he moved the smoke billowed and burned. You cried uncontrollably. Biting and squeezing the blanket. 

Soon he found a rhythm, pulling out farther before slamming back in. His quicker movements actually lessened the pain. 

“There we go.” He gave your cheek a playful slap. 

Playful? There was nothing playful about this. You wanted to be anywhere else. One night stand? What were you thinking? 

SNAP! You lifted your head and squeaked as your bra strap hit into your back. 

“Sorry Y/N.” Sam fisted your bra. “I should have taken this off earlier. I am always awkward with these things.” 

He unhooked your bra while continuing to plow into you ass, speaking in a tone as if you were at a coffee shop. Was he a robot? You bra fell down your arms and he reach around and started kneading your breast. 

“I have always been more of an assman, but I wanted something else to grab.” His fingers tweaked your nipple and pulled down. 

Was that supposed to be a joke? He let out a moan and started fucking you faster. You were a strange combination of numb and fear. You turned your head back into the mattress and bit the blanket. 

“Uhhhh.” He pinched your nipple hard and slammed into you a final time. 

His jizz coated your rectum faster than your tears were falling. It was done. He was done. Maybe he would let you go now. 

You felt his cock twitch a few more times and he let go of your newly abused pebble before sliding out of you. POP. The noise of his exit filled you with a deeper sense of shame. 

It burned. You burned. He stood up and gave your ass a light tap. 

Everything was foggy. You hurt in places you never anticipated hurting. You heard a click and forced your eyes open.

You fell to your side and looked up to see a light on in a bathroom connected to Sam’s room. There was a clear view of him as he started the sink and checked himself out in the mirror. 

Your eyes dropped to the floor. You saw your underwear and shredded dress among his pile of clothing. It was time to leave. He was done with you. 

You needed to be strong. Get dressed and get yourself to the hospital, maybe the police as well. You turned to sit up and winced, tilting to you side to not sit on your abused behind. 

“We are not done.” Sam turned to look at you, his cock was in his hand as he washed it in the sink. 

A whimper left your mouth at the size of it. That thing didn’t even look like it could fit in your correct hole. How was it in your ass? 

“I was thinking I may want to fuck you pussy or mouth next. So I better clean off.” He leaned against the frame stroking himself. “But now I’m thinking your ass was so tight, maybe I will just do it all night.” 

“Please. Let me go. I did what you said.” You pulled your bra back up over your shoulders. 

Sam strutted out to you, his cock already hardening in his hand. He reached down and cupped your chin, then slid his hand down your neck to your strap. You did not try to fight him as he pulled your last garment away and tossed it on the floor. 

“I will let you go. Eventually” He tilted his head. “This is not about you Y/N. It’s not about what you want. It’s about what I need.” 

“You’re a monster.” Tears started to form again. 

“Not a monster.” His eyes danced over your body. “Just soulless.” 

Sam reached down and grabbed your waist, turning you back into the same position. 

“Maybe water as lube will provide a different sensation.” His cock pressed against your aching hole. “Remember. Do as your told.” 

Soulless? You believed it. It didn’t hurt as bad this time. But the pain was still very real as you turned your head and bit the blanket. Willing to do whatever it took to survive. 

~~~ 

The man didn’t sleep. 

You lost count of how many times he anally raped you. You were passed exhaustion, but as soon as you started to doze off he would pinch you nipple so hard you came back. 

Was man even a word to describe him? Monster was more on par. 

Everything was fuzzy. Was this all a dream? 

Knocks echoed through the room. He pulled out of you. Biting the blanket ended long ago and your head was towards the door. Sam cracked it open. 

“What the hell man? We’re waiting on you!” You struggled to lift your eyes.

Through the small crack you saw the blonde brother. Help me. Or was it his turn? You didn’t know so you stayed quiet. 

“I’ve been busy.” Sam gave a happy laugh. 

The same sound that trapped your earlier. Light hearted. Fun. 

“Doing what? Have you slept?” The brother was mad. 

Did he think it was his turn? You let out a whimper. 

“Enjoying myself.” Sam’s voice was familiar, warm, fake. The kind of fake ness only a true sociopath had mastered. 

“IS SHE?” His brother was yelling. 

Sam looked back at you. His eyes sent a fear through you that made you fight the numbness and move your head towards the wall. You were on your stomach, no longer capable of holding your ass in the air. At least he only saw your butt, if any shame was left in you. 

There was some muffled voices. You should have been crying but the tears had long dried. The door shut. You hoped you were alone. 

“A cab will be here in five minutes.” Fabric hit your back. 

Hands were on you, sitting you up on the bed. CRACK! Your jaw ached. Your shoulder’s shook. 

“You did beautifully tonight Y/N.” Same lifted your arms and put a shirt over your head.

You felt like a doll, going with his movements as he stood you up. It wasn’t your shirt. It was his. He stepped you into a pair of basketball shirts. Also his. You wanted to cringe, but felt unable. 

He picked up your purse and through it over your shoulder. Everything hurt and you couldn’t feel a thing at the same time. It was strange. 

“You are a smart girl. I’m sure you know this already, but go to a hospital, call the police, tell your mom, tell your best friend, tell you cat and I will show up and murder everyone you ever loved or thought about loving.” Sam opened the door and started guiding you into the hall. “Do you understand?” 

All you could think about was your own bed. You didn’t want to deal with anything else but resting your body. Sam through his arm around you and picked you up like before. This time you winced as he half carried you down the stairs, his movement reigniting pains. 

He took you straight to the front porch and set you down again. The sun was up. It was morning. 

“Y/N. I need you to say you understand or I won’t be able to let you leave.” 

Everything was moving in slow motion, but you looked back at him. 

“I thought about loving you. Would that mean you’ll kill yourself?” Did you say that out-loud? 

Sam’s doe eyes narrowed and then he broke into a smile and laughed. A yellow car pulled up in front of the house and he walked you down. 

He tucked you in the backseat and paid the driver. Sam didn’t bother to say another word to you before the car pulled away. 

You went on autopilot, getting out of the car in front of your place. You were more zombie than human as you climbed the stairs and passed out in your bed. You didn’t care if you locked the door to your apartment or not. Nothing worse could happen to you. 

~~~ 

Everything hurt worse when you woke up. 

“I’ll murder everyone you ever loved.” 

That line made your eyes pop open. Who had you told? Both your parents! Your best friend! Your mailman! You shouted it from the rooftops!

You sat up in bed only to get thrown back down. Sam’s face looked down at you, blood streaks dripped from his forehead.

“They’re all dead and it is your fault.” He gave his warm smile.

This time you let out a scream and shot up in bed. 

You were hyperventilating and grabbed the brown paper bag you kept on your night stand. Four years. Four years and you still dreamed of that night. 

You breathed into the bag to calm yourself down. If you were lucky it would be enough to pass back out again. But the sun was streaming through your windows and it was time to get up. 

Had it been four years or four seasons? You tried to think of winter, spring, summer, and fall, but they all blended into one. 

The world went to shit, or was that all a hallucination? What did it matter. 

After that night you abandoned everything. You left your job, family, friends. 

Staying would have been selfish. You knew that. All it took to get rid of them was deleting social media and dropping your cell phone. 

One time a PI caught up to you. Said your parents were worried sick. But it was better them being worried than dead. So you told him to fuck off and moved the next day. 

Falling off the grid was easier than you expected. Most mom and pop restaurants didn’t want to deal with the taxes and were happy to hire a waitress under the table. Cleaning houses was an easy gig too. And landlords never minded being paid in cash. 

You put the bag down and grabbed your pair of jeans that were laying on the floor from last night. As you pulled them on you glanced around your one room apartment. 

Before you left for work you made sure your backpack was packed. That was all you needed. The cash, the clothes on your back and a spare. You were always ready to flee. Moving was a necessity in this sort of life. 

Small towns were easier to hide in. People didn’t ask questions. You were ignored as long as you ignored them. But the second you felt uneasy you moved on. 

It had been a month in Iowa and the fear was starting to creep. Maybe you would buy a bus ticket and leave tomorrow. Head on a route to a major town and pick a random stop to get off in. That was the best way to do it. 

You were deep in thought about leaving, starring at the sidewalk when a shoulder bumped into you. 

“Excuse me.”

“Sorry.” 

You spoke at the same time. You looked up and froze on the sidewalk.

All the times you obsessed, thinking what you would have done differently, how you should have fought back, called for help, turned into Wonder Woman and strangled the man with your bra. The small ounces of courage you battled with rushed to you mind. 

But sometimes nature doesn’t change and instead your blood turned into ice as you looked into his eyes. 

“You look familiar, have we met before?” His brow scrunched.

He didn’t remember you. But your breath caught as you re-lived that night again, certain you were screaming but probably being dead silent. 

“Where the hell have you been?” “IS SHE”? 

The blonde. The brother. Dean tilted his head as he tried to jog his memory of the one night you would never be able to forget.


	2. Chapter 2

**Notes for the Chapter:**

> Second Warnings: SUICIDAL THOUGHTS. Please, if you are ever feeling this way reach out for help. The National Suicide Prevention Lifeline is 1-800-273-8255 or visit : www.suicidepreventionlifeline.org they have a chat available if you need immediate assistance. The world is a much more beautiful place with YOU in it.

“You look familiar, have we met before?” His brow scrunched.

He didn’t remember you. But your breath caught as you re-lived that night again, certain you were screaming but probably being dead silent. 

“Where the hell have you been?” “IS SHE”? 

The blonde. The brother. Dean tilted his head as he tried to jog his memory of the one night you would never be able to forget.

“No.” You dropped your eyes to the sidewalk. You had to make a get away, but were certain if you broke into a run he would chase after you.

“I swear I know you from some where.” The man was right in front of you. 

“I don’t think so.” You kept your eyes to the sidewalk. 

You needed to get your bag. Then you would be on the next bus out of town, but if you headed back to your place Dean might figure out where you lived. Was he just as crazy as his brother? Was his brother here? 

You started to shake and brought your hand to your mouth to stifle your sob. 

“Woah woah woah.” Dean’s hands were on your shoulders. 

Everything was happening too fast and your lungs started to burn. You snapped your neck up. His green eyes were filled with concern. You pinched your closed as you gulped in air. 

“Deep breath in.” Dean loudly inhaled. “Deep breath out.”

You did not want his hands on you and you certainly did not want his guidance through a panic attack. 

“Come on Miss.” Dean gave another over done inhale and exhale. “If you don’t take a breath you’re going to pass out. In and out.” 

He was right. Shit he was right. Even though your chest was rattling and it felt like his hands were burning your shoulders you started mimicking him. Forcing your breaths to copy his every movement. 

“Alright. That’s it.” He rubbed your shoulders lightly. “Can I take you somewhere? A hospital? Home?” 

“Don’t touch me.” You stepped back from his grasp. “Just leave me alone. Please let me leave.” 

“Let you leave? Miss what are you talking about?” 

You didn’t want to look at him, but your eyes popped open. His mouth hung with shock and his nose scrunched with confusion. 

“You’re terrified of me.” He frowned and held his hands up. “Wait, I do know you.” 

The tight features on his face started to relax and his eyes watered over. 

“Sam…you were…I’m so sorry. I didn’t know. I should have stopped him.” The water swelled in his eyes and a tear dripped down his cheek. 

You wrapped your arms around your body, a new wave of shame washing over you. 

“I knew something was wrong with him. I didn’t step in. I’m as much to blame as he is.” Dean sniffled. “I’m so sorry.” 

“I haven’t told anyone. Please just let me leave and I won’t tell anyone. You don’t even have to tell him you saw me.” You had to get out of this situation. 

“You’re safe. I promise. I haven’t spoken to Sam in years. Don’t have a clue where he is.” Dean continued to hold his palms up. 

You felt a small relief at his statement, but knew better than to trust anyone. 

“He hurt a lot of people. Myself included.” Dean dropped one of his hands and brought the other to his eye, wiping away the tear. “Could I take you for a cup of coffee?”

Your eyes widened in shock. Never, under any circumstances would you feel bad for this man or willingly spend any sort of time near him.

The realization broke your trance, he wasn’t keeping you here. You were out on the street, free to leave. 

“No.” You turned and started walking away. 

“Please Miss. I could really use someone to talk to.” He walked right next to you.

“Find someone else.” Did you have enough money on you? Could you go straight to the bus station?

“Not many people know what its like to deal with the soulless. Maybe we could help each other find some comfort? Just in talking?” He was hunched down to your height, trying to get ahead of you so you could see his face. 

Could you outrun him? Maybe it would be better to get to a public spot. 

“I am begging you Y/N.” He jumped ahead and spun, blocking you on the sidewalk. “Please, show some compassion.” 

There was only one work you picked up on. Your name. Your eyes went wide with terror. How could he remember it from all those years ago? Sam introduced you that night, but Dean couldn’t even place your face a few moments ago. 

“Aw shit.” Dean’s pleading face smoothed. 

He shook his head and gave a sly smile.

“Used the name too soon?” He let a puff of air out of the side of his mouth.

“What?” Your brain was trying to process the interaction, but all you kept thinking was danger, danger. 

“Fuck it.” Dean grabbed you. 

You opened your mouth to scream, but his forehead smashed into yours before you got a noise out. Your world went black immediately. Danger, danger, your final thought.

~~~   
A dull throb pounded in your forehead. You were groggy with sleep as you stretched. When you tried to pull your arms down your wrists caught. You tried to bend your knees, but they would only move an inch or two off the bed. 

A chill went through you and you pulled all your extremities, but none of them had much give. 

“Wakey wakey.” The voice made your eyes pop open. 

“Mmmfffmf.” You tried to speak, but something was covering your lips. 

You lifted your head and saw your naked body. You yanked your arms to try to cover yourself, but rope dug into your wrists. 

“This is going to be the third time Y/N.” Dean sat down next to you and leaned over. “I’m getting anxious to get started. Please don’t pass out again.” 

You shut your eyes as terror flooded you. Vague memories of the other two times coming to resurfaced. You needed to focus. A hand brushed your cheek and your eyes opened up to see Dean smiling down at you. 

“I’m sure you have a lot of questions, but I don’t really care.” Dean sighed as he stroked your cheek. “I’ve been looking for you for a long time now Y/N. At least six months, but in the back of my mind I think I’ve been looking for you since that night you had with Sammy.

“See, I thought you were beautiful. I was jealous. Then when I got a glimpse of you in the morning, spread out on my brother’s bed, glazed over look in your eyes, I told myself I was concerned. I went to your apartment, but you already fled. Sammy didn’t tell me what really happened for a few months.” 

He moved his other hand to your hair and stroked his fingers over your scalp. 

“We looked for you for a little bit, so Sam could make amends. Let you go back to your old life, but you weren’t the only thing Sam had to atone for when his soul came back and we had bigger problems, but I never forgot about you. Not once.” 

Dean nodded his head as he spoke, almost like he was reassuring himself. 

“Found myself with some free time and really put in the elbow grease. I was so happy the first day I saw you. It was about three weeks. I love the detergent you use on your sheets by the way, almost as much as the sounds of the screams you wake up with every day.” 

You shut your eyes and whipped your head to the side, wanting to get away from his touch. 

“Hey.” He grabbed your chin and moved your head back. “Look at me.” 

You whimpered and did as you were told. The anger on his face melted into a soft smile. 

“You’re a fighter Y/N. And you’re fucking gorgeous.” His hand slid from your cheek to your neck. “That’s why I had to have you and you’re even better than I remembered.” 

His fingers spread out across your chest, above your breasts.

“Plus you keep me on my toes. See today? On the sidewalk? It was all planned. You were supposed to get that coffee, confide in me, and then I was going to get that look of horror when I betrayed you. The same one you gave Sam when he turned on you, it still haunts him. I wanted that. I deserved that. AND YOU TOOK IT FROM ME.”

He pressed down on your chest. Good was all you could think. The anger on his face brought you back to the surface as a realization settled over.

Whatever this man was going to do to you, you could handle. Numbness and fear were your way of living. And if he killed you, so what? Your life wasn’t anything worth running back to.

“So smart Y/N. I love it.” He eased up, and the hand on your face gathered the tape on your cheek. 

Rip. Your mouth stung as the tape was removed. You didn’t scream or beg. Instead you felt acceptance. 

“No ‘help me! Help me?’? No ‘please let me go’?” Dean smirked. “Come on baby, say something.” 

“Do your worst.” You sighed and looked away from him, up at the ceiling. 

“I love it Y/N!” Dean rose from the bed and clapped. “Sammy did such a number on you that you don’t care! Not if I chop you up into little pieces or burn your with an iron or even if I buried you alive. Such a challenge to torture a broken person. Really entertaining stuff.” 

He was taunting you, but it wasn’t worth his time. There was no chance you were going to react to any of his threats. 

You concentrated on the ceiling. It was cement. You were in a basement. Not that it mattered. You doubted you were going to get out alive. 

Soulless wasn’t a thing. Everyone had one. Sam was just a monster, and just as you assumed, his brother was to. It was only a matter of time before he caught up to you. Maybe when Dean was done you could finally find some peace. 

A strange sensation broke your thoughts. You let out a gasp and lifted you head to see Dean’s face between your legs. 

He dipped back down and ran his tongue over your slit, all the while grinning up at you. 

“Now there’s a reaction.” He placed a light kiss on your clit, sending a chill through you. “Tell my baby, when was the las time you came? It certainly wasn’t with my brother. Have you been able to touch yourself since?” 

“What are you doing?” You tried to push your hips into the bed, away from his mouth. 

“Such a pretty pussy.” He spread your lips with his hand, studying you. It made you pinch your eyes shut, unable to comprehend his plan. 

“I bet you’re corked, prime for popping.” He kissed your thigh as he lifted his head, still keeping you spread. “Let’s make a deal.”

“Fuck you.” Tears stung your eyes as the tingling between your legs grew. Why were you responding? What horror did he have in store? 

“All in due time.” Dean gave a chuckle. “Come on, let’s play. I think either way you’re going to end up a winner Y/N.”

You opened your eyes but kept them trained on the ceiling and tried to zone out. But before you entered any form of safe space a finger entered you.

“Ahhh,” you gasped and arched your back.

“So tight. Like a virgin, but with the drive of a whore.” Dean curled his finger inside of you and another chill went down your spine. “Five minutes Madge.”

Five minutes until he killed you? You’d take it. He pulled his finger out slowly and you felt it drag on your walls, forcing you to bite back a moan. 

“Madge?” Dean pushed back in and started flicking his finger, making it harder to hold back the moan. “The clock doesn’t start until you agree Madge.” 

Agree? You didn’t understand, but you didn’t want to engage. 

“Alright. Accepting defeat Madge. I can take it.” Dean increased the pressure on his finger and his mouth dropped to your clit. 

He sucked it between his lips and you pulled at your bindings, trying desperately to shut your legs. 

“Wrong girl.” Your hips twisted, but you didn’t have enough leeway to get away. 

You regretted speaking briefly, but when his mouth left you were grateful. 

“Oh you’re my personal Madonna.” Dean smiled. “Now Madge, are you interested in a way out of this?” 

“Yes.” His finger was still in your pussy and you squirmed as it stilled. 

“If I don’t make you cum in five minutes I will let you go.” Dean’s finger started curling inside of you again and your body stopped moving. “Actually, I’m feeling generous. Let’s make it three.” 

“What?” Your head was getting fuzzy. 

Dean ignored you and dipped his head back to your clit. 

“STOP!” Why the hell did he want to make you cum? Wasn’t he going to kill you? 

He sucked hard and his tongue flicked back and forth as his finger started working into overdrive. 

“NO!” You bucked your hips away from him, but he was on you like glue. 

A rush of heat went up your body as Dean started to hum. The sensation was too much and it didn’t take much for the moan to break free. 

“That’s it Madge.” His finger continued its assault and now you found yourself moving with him as you panted. “So fucking beautiful. Cum for me.” 

“I…I…”. You meant to say ‘I don’t want this’. But the words never made it out of your mouth. 

He resumed his place on your bundle and his tongue started moving so fast it felt like a vibrator, hurdling your body into overdrive. 

As he sucked on you all the peace and clarity went out of your body along with the fear. You couldn’t remember the last time you felt any semblance of pleasure. Dean was right, you were pent up and your eyes rolled into the back of your head as your orgasm erupted. 

Your body shook and tingled while your soul felt like it was hovered above the bed. Your head lulled to the side in ecstasy as your muscles tightened and relaxed in rapid spurts. 

“Not even a minute Madge.” Dean lifted his head and pulled his finger from your pussy. “I win.” 

He grabbed your chin and turned it to face him. One glistening finger was held in front of your eyes and you cringed, knowing it was your own wetness. 

The euphoria from the orgasm left and was replaced with shame. How could you orgasm tied down like this? With a stranger? 

Dean’s green eyes had a twinkle to them as he placed his finger to his mouth and sucked off the juices. 

“Win? What do you want with me?” 

The orgasm awakened your senses and the one that poured back in was fear. 

“Well I want to torture you. I thought I made that clear.” Dean got up from the bed and pulled off his shirt. 

“Chop me up? Bury me alive?” You rolled your eyes and took a deep breath, maybe you should be grateful for the orgasm. 

“Na, I’m going to show you what a whore you are Madge.” Dean dropped his pants. “I’m going to make you cum again and again, until the only thing in this world you want is my cock. And when you’re a sniveling mess, begging for it, you’re not going to just be a whore. You’re going to be my whore.” 

“Never.” Your voice shook as his threat settled in. 

“What sort of girl has an orgasm from a rapist? From the brother of her rapist? Only one that’s begging for it.” Dean’s cock sprung forward and you tried to shut your legs again, terrified of how excited you were at the size of him. “How many times do you think I can make you cum before you pass out? Let’s try for eight.” 

“I have no control.” You tugged at the bindings on your wrists. “It’s my body’s reaction.” 

“Exactly. Because you’re a whore Madge.” Dean got on his knees between you, fisting his cock as he lined up with your entrance. 

“NO!” You turned your head to the side. 

“Oh Madge.” 

Dean pushed forward and you whimpered, still too fresh from your orgasm. Every nerve in your body lit up as he filled you. You were certain you drew blood biting your lip trying to stifle the moan. 

“That’s right baby, the harder you fight the harder you’ll cum.” Dean put one hand on each side of your head as he started rocking into you. “I’m going to get that glassy eyed look and then you will be mine forever.” 

His words shook you. Why was he doing this? It didn’t make any sense.

“You’d like that wouldn’t you baby? Being mine? No more running, no more hiding, just being a good girl and taking my cock, cumming again and again?” His face was right next to your ear as he bottomed out inside of you and came to a halt. “Admit it Y/N, and I’ll let you cum.” 

“Never.” As much as your body responded to him you weren’t insane. 

“We have all the time in the world Madge. I’ll change your tune.” He pulled out and then slammed back into you, stopping to grind his pelvis against your clit. 

You didn’t have time to think before your body reacted and you thrusted your hips against him. He leaned down and licked your neck. 

“Like the finest champagne, ready to pop again.” He barely pulled out as he started rubbing up and down, sending your clit into overdrive while his cock edged in and out of you. “Pop baby.” 

You cried out as another orgasm came over you. Dean grunted and slowed his hips to a roll, putting pressure against your clit, making your toes curl and your eyes dance while your vision blurred. 

“That’s two Madge. And I’m not even close to blowing. Eight? I’m think Eleven now.” Dean bucked his hips back and slammed back inside of you. 

“Why?” As the orgasm died your clarity briefly returned. “Why?” 

“Why do you think?” He grazed his teeth on your neck as you went limp. 

Your time with Sam felt like yesterday, but it was so different from this. Dean was so interested in your pleasure, while Sam made it clear it was never a priority. 

“The soulless only care about themselves.” You weren’t sure you said your thought outloud. 

“No, the soulless don’t care if they hurt you.” Dean lifted his head and looked down at you. 

Pitch black eyes sent ice through your body and you let out a scream. Dean just smiled. 

“While a demon WANTS to hurt you.” He licked his lips and then started pumping in and out of you slowly. “And nothing will hurt you more Y/N, then showing you what you really are. The type of person who cums with a devil.” 

He dropped his head and started railing into you. Demon? Devil? What was happening? There was too much information to process that your brain scrambled and in that moment your body took over. 

Before you knew it as happening another orgasm started to build. You didn’t have the time to stop your noises as Dean’s thick cock rammed in and out of you. The coil in your stomach tightened and tightened. 

There was no time to fight it and the spring inside of you ignited. You moaned, grunted, whimpered and cried as the release settled over you. The sound of Dean’s body smacking into you was too much and you came again. 

“That was number three Madge.” He looked down at you with his green eyes again. “Eight more to go before I let you rest.” 

Were you hallucinating? Was this even real? Did your brain break? A huge grin crossed Dean’s face. 

“That glassy eyed look. All mine.” He flexed down hard and your back arched. 

What the hell was happening to you?

~~~

There was a haze over everything. You were covered in sweat and whenever your body started to go numb Dean found a creative way to bring you back. Right now he was sucking on your neck, why did it have to feel so good? Why were you even fighting? 

“Approaching ten Y/N. Are you ready to admit you’re mine?” He pressed his forehead to yours. “Be my good whore?” 

You weren’t a whore. You hated your body. You hated yourself. But hallucination or not, you were still you. 

“So close Made.” Dean sucked in a huge breath. “Break for me. You want to. We both know it.” 

You whimpered and turned your head as his hand went between your bodies and started fondling your clit again. You were raw. If you admitted you were a whore would he stop? Probably not, he would keep going just to prove it. 

He gave you a feather touch and you winced, the line of pleasure and pain had almost disappeared. 

“Say it baby. Be my whore.” Dean licked up your cheek. 

Why you? What did you ever do to deserve this? 

CRACK! A loud sound filled the room followed by a whoosh. 

“Came to join the party?” Dean’s voice sounded like an echo. 

His cock left your hole and you gasped. A strange emptiness flooded you and there was no way to tell if you were grateful or miserable at his disappearance, but either way you had a chance at sleep and even your over eager body welcomed it. 

Consciousness started to drift away as the new voice yelled out in Latin. THUD. You didn’t know if it ws the sound of your head dropping back or something hitting the floor.

“Y/N?” Someone was over you. “Oh God, what did he do to you?” 

Hands were on your binding and pins and needles filled your hands as the ropes were undone. The sensation made you open your eyes. 

You thought your brain had become mush but the sight of the person in front of you brought nothing but sheer terror. 

Sam had arrived. 

Dean thought he had broken you, but seeing his brother sent you a jolt back to reality. The sound of your scream echoed in your ears as reality left. Blackness took you and this time you hoped it was for good.

**Notes for the Chapter:**

> Second Warnings: SUICIDAL THOUGHTS. Please, if you are ever feeling this way reach out for help. The National Suicide Prevention Lifeline is 1-800-273-8255 or visit : www.suicidepreventionlifeline.org they have a chat available if you need immediate assistance. The world is a much more beautiful place with YOU in it.


	3. Chapter 3

Nothing hurt. In fact when your eyes fluttered open you felt more rested than you had in years. You stretched your arms over your head and flexed your back. 

 

“Good, you’re awake.” The voice sent a chill down your spine. 

 

You popped up in bed and crawled into the corner. Your eyes scanned the room. It looked…normal, but instead of taking in the décor you looked for the door. Of course there was a chair right next to it, and seated was the man who had plagued you for years. Who had destroyed you. 

 

If you stared at him you would lose it. In fact, your body already started to shake. Memories of your night together, how he hurt you, used you, threatened you. You bit your lip to stop from screaming. 

“I can never make up for what I did to you.” Sam ran his hand over his hair and sighed. “Or for what Dean just did.” 

Dean. You had forgotten about him, even though it was hours ago. You pinched your eyes shut and clawed at the wall behind you as memories of him between your legs, forcing you to cum over and over again, brought on the shame. How many times did he make you orgasm? Was that why you were so relaxed? What was wrong with you? 

“I will try and explain it all.” Sam stood up. “But I have to fix him first. I don’t expect you to believe me, but your interactions with us, that’s not who the Winchesters are.” 

 

“Let me go.” You wouldn’t look at him as your chest heaved. “I never told anyone. I’ll never tell anyone.” 

“You’re not a prisoner Y/N.” Sam’s voice brought you no comfort. “Once I cure him, bring the real Dean back, there will be nothing for you to fear. You can go back to your old life or build a stable new one. You’ll see.” 

You wanted to believe him, but memories of that night he picked you up at the bar reminded you of that mistake. You would never trust anyone again. 

“There’s a shower in here.” Sam pointed over his shoulder. “Dean will become human again, just like I got my soul back. Then we will set you up, but right now…I need you to stay here.” 

“NO!” You curled your legs into your chest and opened your eyes. “Just let me go!” 

 

Pain was the word you would have chosen to describe Sam. His brow creased and eyes were filled with forlorn hope. For a split second you doubted your doubt. 

“Soon. I promise. This is for your own good in the long run.” Sam opened the door. “This will be over soon. You never have to see either of us again.” 

 

You threw your body forward on the bed as he left the room, slamming the door behind him. Your hands went to the knob and you tried to tug. Locked. 

Trapped. You were locked in here. With open palms you slapped at the door. 

“PLEASE!” You sobbed and sunk to the floor. “I’ll never tell! Let me OUT!”

Nobody was on the other side. There were no windows in the room. There was no way out. 

Time felt like an illusion. You didn’t know if you sat on the floor for five minutes or five hours. The first of your senses to return was smell. The room reeked of Sam, the similar scent of the night he destroyed your life. But you, you smelled like Dean. 

He had forced orgasm after orgasm onto you. Your brain tried to fight them, but your body had other ideas. You dropped the arms that were clutching your shoulders, unable to even touch yourself. 

Shower. If you could wash him off you would feel better. Your brain shut off and you ran to the bathroom, grateful as you turned on the water and stepped into the tub. 

 

You didn’t take off your clothes or care about the temperature as icy water blasted you. When the wet t-shirt clung to your skin you realized it was one of the Winchester’s and the fabric might as well have been made of maggots. 

You ripped them off as fast as you could and then cranked the temperature up, hoping to sanitize yourself as you started to scrub. Not allowing yourself to think about anything but getting clean. One step at a time.

~~~

After the shower you could not bring yourself to go through Sam’s drawers. You would not wear an article of their clothing. Somehow the towel felt cleaner, so you wrapped it around yourself. It was oversized, but that wasn’t necessarily a bad thing. 

The door wouldn’t open. You had no choice but to wait. Maybe Sam was telling the truth. He did look genuine. Maybe they would come and let you out. Then you could go home, see your family, your old friends. 

The idea brought a smile to your face. Of course you knew it was a fantasy. It was more likely this was some form of torture the brothers got off on. You never believed Sam lost his soul, not really. But Dean’s black eyes…that was inhuman. Were they telling the truth? 

Hope was always easier to concentrate on then defeat. Even though every ounce of your being told you not to, you chose hope. Because the other option would drive you insane. You would get out of here. You would. 

Those thoughts passed through your mind on repeat and again time slipped away. How much longer would it be? Maybe you were dead and this was hell. 

~~~

The door flung open. If you were capable of throwing up your heart you would’ve at that moment. Dean stood in the frame, breathing deep. His expression melted and mirrored his brother’s earlier pain. 

“Y/N.” He held out his hands. “We’re going to get you out of here.” 

 

He started to back up. The open door was so tempting, but was he going to grab you? Was this a trap? Your circle of thoughts came to a crashing halt. You had no clue what to do. 

 

“Sammy never should have brought you here.” Dean moved all the way into the hall. “I won’t touch you. Nobody will bother you ever again. I promise.” 

Your feet moved slow, but you went in line with the door. The guilt on his face made you look at the floor. You couldn’t trust him. Never. But this was your only chance of escape. 

“The last door on the left.” Dean’s voice made you look up. He pointed the direction. “That will take you to a set of stairs. Take them up. You never have to see either of us again. I’m so sorry.” 

Sorry? He was sorry? He made you feel like an animal! Then the caging in this room. If they were human, were you? After what the two of them had done to you you felt more like a shell. Hope. You had to cling to it. 

If this was your chance you weren’t going to waste it. Before you overthought you took off running, taking the doorframe too tight and banging your shoulder into the wood. You ignored the pain exploding in your bone and ran. 

The hall was long, lined with doors and no windows. What sort of home was this? It didn’t matter. Nothing mattered but that last door on the left. Your eyes focused on it and you picked up speed, pushing your body as hard as you could. 

When you arrived your lungs burned, but you flung it open and readied to jump up stairs two at a time. Instead you saw Sam standing there. You were running too fast and unable to slow down as you smacked into him. 

He grabbed your arms and held you up. What? How? Where were the stairs? All you saw was a giant bed. You looked at Sam, the man who plagued your nightmares for so long. He had a blank look on his face. 

“What?” Your breathing was so heavy you couldn’t form a sentence. 

 

Sam slowly lowered you to the floor. Your knees hit the tile in front of him while your brain started to fire. You didn’t know what was working in overdrive, your head or your body. 

ZIPPPPPP. The sound of his fly going down brought you back to reality.

“ENNNGGHH!” You shrieked, realizing the position you were in, kneeling in front of the brunette. 

Your hands went to his thighs, ready to use them to push yourself off and stand up to run again. Mistake number million as his hand grabbed the back of your head and pushed down keeping you in place. 

 

His cock tumbled out of his pants and smacked you in the face. Your shoulders trembled with your cries, but his hand grabbed your chin and yanked it down. 

“Bite and you’ll regret it.” Sam kept the blank look as his other hand grabbed the base of his cock and shoved it past your lips. 

Your mouth was dry and he was rough on your tongue. You reacted by trying to spit him out, but that gave him easier access and made saliva start to pool at the back of your tongue. 

“I always wondered how your mouth and pussy felt.” Sam yanked your head forward, forming a fist in your hair. “Thought it was a mistake sending you home. I should have locked you in the closet like a good doll.” 

The more spit you could form the easier you could handle him. You flicked your tongue back trying to generate more. 

“MMMMMM.” He brought your head down further. “Even better than I imagined.” 

“Her pussy is like heaven.” Dean’s voice made you quiver. “That’s a real compliment Y/N. We’ve both been there before. And I’d rather be inside of you.” 

His hands touched your shoulders and more pressure was on your head as Dean pushed you further down Sam’s cock. It was salty and you wanted to shut your mouth, bite him, but fear of what they were capable of made you relax your jaw as he shoved deeper. 

“You’re a smart girl.” Dean’s hands trailed down your back. He grabbed the towel and yanked it away with ease, leaving you naked. “But you’re also a little slut. Did you really think we were going to send some poor girl outside in the middle of nowhere wearing a towel? I expected more from you. But I think you knew what was in store for you. And you wanted it.” 

NO! Dean didn’t understand how confused you were, how desperate. 

“Don’t worry. Me and Sammy are going to deliver everything you want Baby.” Dean’s hands cupped your breasts. His fingers wasted no time finding your nipples and tweaking them. “You’re not even fighting us. Did we break you that much already? No wonder you’re so perfect for us.” 

He was right. Your hands were still on Sam’s thighs as he continued to fuck your mouth. You could fight. Escape. 

At the same time you moved your fingers to push Dean away his hands both moved to the back of your head and shoved it down. 

Sams cock hit the back of your throat and you started gagging. You went back to his legs and tried to push yourself away. 

“Fuck. That feels good.” Sam’s cock started to pulse. “She’s swallowing me.” 

You could barely breath and if there was food in your stomach you would’ve puked all over him. You took in a huge breath from your nose and tried to ignore the burning in your throat when Dean reached around and plugged your nose. 

All oxygen was gone and you scrambled to get away. But Dean held you in place while Sam’s cock suffocated you. 

“Y/N. I need you to listen. I know Sam told you he was going to fix me. But he lost. What do you think he gambled. Do you think he’s a good enough brother to bet something, like say, his soul?”

 

You heard Dean, but were trying your hardest to get out of this position, unsure if you were going to die by suffocation or some other form of later abuse. But you nodded your head.

“Such a good listener.” Dean chuckled. Sam let out another moan. “Well Sammy lost…or did he? I think if you be a good whore all three of us will be winners tonight. Do you understand?” 

YOU NEEDED AIR. You nodded your head, eager to agree to anything. Sam pulled out a little, but Dean did not unplug. The rush of oxygen made your throat burn, but you tried to gulp it down. 

“Fuck.” Sam pushed forward again, making you cough. “Her mouth is amazing.”

“Remember.” Dean crouched down behind you, so his lips were next to your ear. “The soulless don’t care if they hurt you. Demons want to hurt you. All I’m after is getting you to admit you’re my whore. Are you ready to give over to that? Or should I leave you alone with my brother?” 

Sam’s cock was choking you. You would not survive this. You would not survive them. As always your body was ahead of your brain and your head started to nod. Then you switched to shaking it from side to side. NO!

“I’ll take that as a positive step.” Dean licked up your neck before standing back up again. “Finish in her mouth. Then it’s my turn for a shot at that ass.” 

Sam pulled out all the way and your body fell forward, certain you were going to puke on the floor. But then Sam’s cock was back in your mouth right away. He grabbed the sides of your head and started pushing your skull back and forth. 

It hurt and you struggled to form enough spit to keep up with his thrusts. Your noises turned into gurgles as he used your mouth without concern. 

You couldn’t keep up and just stopped trying. 

 

“There she goes.” Sam grunted and pulled you down harder. “I’m getting in much deeper now.” 

 

“I’m telling you Sammy, it can be so much better when she is involved.” Dean ran his hand down your back, but you were too concentrated on the burning in your throat and desperate attempts at oxygen to even pay attention. 

 

Then you felt his finger slide between your ass. You started to scream and tried to get out of Sam’s grip, but all you got was an approving grunt from Sam. 

“You might be right.” He looked past you. “These struggles make a new sensation.” 

 

“Wait until you feel her cum.” Dean’s finger stopped right at your tiny back hole. “That’s when you really get a taste for her.” 

 

You tried to clench down, desperate to keep him out. That night with Sam was years ago, but it was the cause of all your problems. You would never let anyone near your behind again and tried to twist away. 

 

Dean’s hand grabbed your hip and then he moved so his mouth was near your ear. 

“Want to hear a secret Y/N?” His finger darted lower and found your pussy. 

He pushed inside of you and your mouth opened further around Sam’s cock in surprise. The younger Winchester used that as an invitation to slam his dick further down your throat renewing a round of coughing and gagging. 

But Dean’s finger wiggled inside of you, curling against your sensitive walls. 

“Feel that?” Dean’s smile carried through his tone. “You’re wet baby girl. This is turning you on.” 

 

Horror flooded your mind. How? Why? It wasn’t true, but you couldn’t deny how easy his finger slid inside of you. 

 

“Soaked even.” He pressed down and rubbed the fleshy patch inside of you. 

Fuck. It felt good. Why did it have to feel good? Dean’s other hand wrapped around and his thumb pressed against your clit. 

 

“Mggppff!” You tried to swat Dean’s hand away, but all it did was make Sam increase his speed without the little resistance your palms on his thighs was providing. 

 

“Damn.” Sam grunted. “Make her moan again.” 

Moan? Were you moaning? All you could hear was the gurgles coming from the deep throat you were getting. 

 

“Oh I’ll do better Sammy.” Dean started rubbing circles on your pearl while his other hand started to finger fuck your pussy. 

You couldn’t focus on any one thing. You tried to wiggle your hips to get away from Dean’s touch, but any attention you didn’t pay to lessening Sam’s force resulted in him going even further, bringing on a new burning pain. 

“Mmmmm.” You heard it that time and hated yourself. 

“That’s it Lady.” Dean increased his speed. “You’re so hungry. Hungry for my brother’s cum and your own pleasure. Just give in, be a good little slut.” 

“Ughhh.” Your eyes rolled back in your head as the pleasure exploded over your body, the orgasm powerful enough you began to tremble. 

“Shit.” Sam slammed your head down and held you in place. 

You couldn’t breath, but all that did was make your other senses higher and it was like the orgasm resurged. Then you felt Sam’s cock flex in your mouth, but he was so far back you didn’t taste a drop of his cum and he sprayed it straight down your throat. 

“You were right.” Sam pulled his cock out and Dean’s hands vanished. 

You fell forward, a coughing crying mess. You gulped in air. 

“It does feel better when she’s into it.”

 

How could you have came during that type of treatment? Demon or soulless it didn’t matter. They were monsters. Even if their excuses were lies.

A hand wrapped in your hair and you brought your hands up to grab the wrist and stop the pain of the pulling as you were yanked to your feet. Sam was in front of you, undressing with a blank expression on his face. 

“See that bed?” Dean other hand gripped your hip and ran up your side before dipping over and tweaking your nipple. “That’s your new home Girly.” 

 

He pinched your tiny bud hard making you cry out. 

“Now, do you want to be tied down again?” He lessened the pressure. “Or do you want to behave?” 

You got the message. You’d experienced one night of nothing but pain with Sam and nothing but pleasure with Dean. There was no doubt which one was preferred. 

“I’ll behave.” You hated yourself. 

“I still expect some fight from you.” Dean dropped your hair and moved both of his hands to your back, shoving you onto the mattress. “But that’s a positive step. I’m proud of you Baby.” 

There was no way out of this. Why you? When would they stop? What did they want? Then your remembered: Dean wanted you broken. Well you could break. 

“I’m a whore. I’m a slut. I’m whatever you want me to be.” They were just words. 

“Wow, that was a personality change.” Sam laughed. “Does that mean night’s over?” 

“That means miss Y/N here is a liar.” Dean was behind you. He pressed you down so your were flat on your stomach and pulled you backward, tucking your legs underneath you in the process. “But I like the enthusiasm.” 

“Please. I admitted it.” You cried, knowing how vulnerable the position made you. “You said that was what you wanted. I’m broken.” 

“Na, see if you were broken you wouldn’t care that I was about to fuck your ass.” There was a cool gel squirted between your cheeks. “And if you were ready to accept that you were in fact my whore, you would be excited about me fucking your ass.” 

“Anything else.” You couldn’t take this. You darted forward on the bed to crawl away. 

“Sammy!” Dean grabbed your ankle and yanked you back. “Pin her down.” 

You tried to kick out, but Sam was on your in a second, pushing your shoulders into the bed while Dean put you back in the same position. 

 

“I was going to start slow with you Y/N.” There was the sound of more lube being applied. “But for that little outburst I don’t really see a point.” 

“PLEASE DON’T!” You sobbed into the blanket. “NO!” 

“I love when you beg.” Dean’s cock pressed against your tiny hole and you started to shake. “Relax and it will hurt less, but either way it won’t hurt for long.” 

You cried in defeat as he nudged against you. The weight of the bed sank and you were incapable of keeping him out. His cockhead broke past, stretching you and making you grunt. You ground your teeth so hard you thought they might shatter and moved to biting the blanket. 

“Sam, you were right it is nice.” Dean pushed forward, splitting you further. 

You arched your back and cried out. Then you tried to claw forward again, hoping for any type of escape. But Sam was holding you way too tight and you didn’t move at all. 

“Half way there.” Dean grunted. “It’s even too tight for me. I’m working up a sweat here Baby Doll.” 

Half way? It felt like he was deep in your intensities already. How were you supposed to take more of him. Then you felt it a fingertip at your clit again. You tried to bend your arms to swat it away, but Sam easily gathered your wrists and held them above your head while holding you with his other hand.

“You’ve never came with something in your ass before have you?” Dean chuckled while he lazily stroked your clit. “Well we will have to change that.” 

He continued his decent into your rectum and began flicking your bud. You hated it because you were swelling underneath him, like that piece of your anatomy was eager for his attention. Dean groaned as he pushed in further.

“OW! It hurts!.” You sniffled and wondered why you said that. Neither of them cared.

“Maybe I will make you my anal whore Y/N.” Dean grunted. “Make it so you can only cum when something is in your ass. Would you like that?” 

You cried and didn’t respond to his taunt. 

“It won’t always be a cock of course, sometimes a finger, maybe I’ll get you some toys?” Dean entered farther and picked up his attention to your pulsing clit. “I’d love to watch you fuck yourself up the ass. You’ll be happy to jam a vibrator up there because it’s the only way you’re allowed to cum.” 

The image of you masturbating like that came to mind and you didn’t know why, but it was degrading another wave of wetness came to your pussy. 

“Oh, you like that idea?” Dean laughed. “I felt your ass clench up a little at the thought. Well if that’s what my anal whore wants, that’s what she’ll get.” 

He started rubbing faster on your clit and you didn’t know which sense was more powerful, the pleasure from his fingers or the burning from his cock. 

“Mmmmm.” A moan broke from your mouth. 

The bed moved and Sam slid his hand up to your head and turned it toward him. His cock was right in front of your face again, rock hard. The sight made you whimper. 

“Wait your turn brother.” Dean continued to stretch you. “Besides, I think there’s still a different hole for you to try next.” 

“Thank you.” You winced as soon as the phrase left your mouth. 

Both Winchesters laughed. 

“Oh you’re welcome Baby.” Dean slowly pushed further and then your felt his pelvis on your ass. You’d taken all of him. “Being so polite like that earns you a reward.” 

He had bottomed out. You couldn’t believe you’d taken all of him. His fingers started to work your clit with vigor and you didn’t even attempt to bottle up the noises. What the hell was wrong with you? You found yourself moving slightly, almost humping Dean’s hand, making his otherwise still cock fuck your ass. 

This time when your orgasm hit it was like flying off a cliff, but instead of falling you went higher and higher. Your empty pussy clamped down on nothing, but your ass responding in a similar manner, flexing against Dean’s cock. 

The pleasure mixed with the giant invader and tingles covered every ounce of your being. 

“Beautiful work Y/N.” Dean’s hand vanished and his cock pulled out before slamming back into you. 

“UMF!” You groaned into the bed. 

“You’re like a fucking vice.” Dean moved back further this time and his re-entry made you shake. 

It didn’t hurt. That was almost worse. In fact, it was a strange sensation. Something you never thought you would get used to. You cringed when you realized it wasn’t getting used to. It was enjoyment. It felt good being so stuffed. 

“Oh you’re getting into it.” Dean leaned over your back and you realized Sam had let go. 

You were caged by Dean, but weren’t even trying to get away. There was no reason for his to hold you. 

 

You looked up at the brunette to see him stroking his cock, eyes glued to you while Dean plowed into your asshole. Warm tears stung your eyes at the shame of it all. 

“Alright. I think I’ve worked you out enough.” Dean grabbed your hip and rolled, taking you with him. “You can get in the fun now Sammy.” 

“What?” You looked at the ceiling and realized what Dean meant. “NO!” 

You tried to get off of him, but his cock was buried in your ass, and he held you down tight. Before you could even sit up Sam was looming over you, pushing you back against his brother’s chest. 

“I CAN’T PLEASE!” You tried to claw at the bed, and shut your legs, but nothing worked. 

Sam was lining up with your pussy. You tried to hit him, but nothing landed or seemed to bother him. 

“It’s okay Baby.” Dean regrabbed you so both of your arms were pinned down. He also bent his knees, spreading your legs outside of them. “We’ll both fit. Don’t worry.” 

You started to sob again and turned your head to the side. Sam’s cock slid inside of you and it made you scream. 

This was more painful than losing your virginity had been. Dean in your ass made you way too tight and you felt every inch of Sam. They were literally splitting you open. 

“Look at the bright side.” Dean kissed your neck. “Your ass is still stuffed so you’ll get to cum again. Maybe a few times if you’re really good.” 

“Fuck! I hate you! Shit! Stop! It hurts!” Your body shook. “It hurts!” 

“Can you shut her up?” Sam looked annoyed. 

He was not nearly as slow as Dean had been, but was still far from fully sheathed. 

“I like the noises.” Dean squeezed you tight. “If you want her quiet, give her a kiss.” 

You turned your head to the side, never would you allow that, but Sam’s hand grabbed your chin and he moved your face back pressing his lips to yours. 

You grunted and tried to move away, but there was nothing you could do. You felt Sam bottom out, but he wasted no time pulling back and fucking you. 

Dean pretty much stayed still, occasionally Sam’s thrusts made you bounce on his brother’s cock, but for the most part all Dean did was make you tighter. 

 

“Fuck her pussy is good.” Sam lifted his head. 

“Wait until you feel her cum.” Dean kissed your neck again. “I’ll help.” 

Sam pushed off of you so that he was on his knees, his cock still drilling into your pussy. Dean dropped one of his arms and slid it down, paying attention to your clit. 

“I figured out a few tricks tonight.” Dean gathered some of your wetness and moved back to your bud. “She’s so sensitive here and if your rub this way.” 

Pleasure started forming even with the pain. You gasped and found yourself taking Sam easier. 

“She can barely last a minute.” Dean’s fingers were working some sort of magic on you.

You tried to lift your head to see what he was doing, but you were distracted by the view of Sam’s cock slamming into your quaking pussy and it was so erotic you couldn’t help yourself and the trembles of the orgasm started to form. 

“There she goes.” Dean laughed. 

It felt good. No, it felt amazing. You didn’t even think about Dean’s words when you erupted again. 

“Fuck.” Sam groaned and he sped up. “URG.” 

 

He pressed down into you and exploded in your pussy. You couldn’t stop him or yourself as the orgasm turned you into complete mush. 

“She on the pill?” Sam pulled out of your pussy. 

It was still spasming from the ecstasy and you whimpered at the exit. 

“No.” Dean rolled you over again. 

You weren’t capable of forming a coherent thought as he pulled you back. Positioning you so your ass was in the air and he was on his knees. 

 

“But I’ve been stalking her for awhile.” He slid out of your ass and re-entered with ease, pushing you into the mattress. “She’s not ovulating, just ended her period. I’ll get her started on some meds next cycle.” 

 

Next cycle? Dean grabbed your waist and then started fucking your ass. You gave no resistance whatsoever as you stretched and contracted around his cock. 

 

“Alright.” Sam’s voice faded. 

In fact everything started to fade. Your vision began to go black when you felt a tingle coming from your pussy. It made you moan and brought you back to reality. 

 

“Come on now Lady.” Dean was plowing into you, but his finger had found your clit again. “When your ass is filled you get to cum. I want you to take advantage.” 

You whimpered, and realized your mouth hung open and drool was making your cheek wet. Instead of fighting it you rolled your eyes into the back of your head as another wave of pleasure came. Was it a new orgasm or a continuation of the old one? You didn’t know, and you weren’t capable of fighting. 

“There it is.” Dean grunted. “That glassy eyed look. Perfection.” 

He slammed down one final time and blew inside of you. As he finished inside of you one thought came to mind: for the first time in as long as you could remember, you weren’t afraid. And that should have terrified you.


End file.
